Photocaged Competitor Guests: A General Approach Toward Light-Activated Cargo Release From Cucurbiturils

Miguel A. Romero, Nuno Basílio, Artur J. Moro, Mara Domingues, José A. González-Delgado, Jesús F. Arteaga, Uwe Pischel

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

A general approach toward the light-induced guest release from cucurbit[7]uril by means of a photoactivatable competitor was devised. An o-nitrobenzyl-caged competitor is photolyzed to generate a competitive guest that can displace cargo from the host macrocycle solely based on considerations of chemical equilibrium. With this method the release of terpene guests from inclusion complexes with cucurbit[7]uril was demonstrated. The binding of the herein investigated terpenes, all being lead fragrant components in essential oils, has been characterized for the first time. They feature binding constants of up to 108 L mol−1 and a high differential binding selectivity (spanning four orders of magnitude for the binding constants for the particular set of terpenes). By fine-tuning the photoactivatable competitor guest, selective and also sequential release of the terpenes was achieved.

Original languageEnglish
Pages (from-to)13105-13111
Number of pages7
JournalChemistry - A European Journal
Volume23
Issue number53
DOIs
Publication statusPublished - 1 Jan 2017

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Keywords

  • chemical release
  • cucurbiturils
  • photochemistry
  • supramolecular chemistry
  • terpenes

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